Self‐assembly of daisy chain oligomers from heteroditopic molecules containing secondary ammonium ion and crown ether moieties

Abstract

AbstractMALDI‐TOF MS of the heteroditopic compound 2‐(benzylammoniomethyl)dibenzo‐24‐crown‐8 hexafluorophosphate (4) revealed oligomeric “daisy chain” species up to the hexamer. Similar results were obtained for 2‐(6′‐hydroxyhexylammoniomethyl)dibenzo‐24‐crown‐8 hexafluorophosphate (8). The complexations of two substituted dibenzylammonium salts, 2,2′‐dimethyldibenzylammonium hexaflurophosphate (9a) and 2,2′,5‐trimethoxydibenzylammonium hexafluorophosphate (9b), with dibenzo‐24‐crown‐8 were examined as models for slippage systems; association constants are reported for these systems. A crystal structure is reported for the new dimethylbenzylammonoium pseudorotaxane. The trimethoxy analog is shown to be capable of slippage formation of a rotaxane, albeit in low yield. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 975–985, 2010